Paniculoside IV - Compound Card

Paniculoside IV

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Paniculoside IV

Structure
Zoomed Structure
  • Family: Plantae - Asteraceae
  • Kingdom: Plantae
  • Class: Glycoside
    • Subclass: Ent-Kaurane Glycoside
Canonical Smiles OCC1O[C@@H](OC(=O)[C@]2(C)CCC[C@@]3([C@@H]2CC[C@]24[C@H]3CC[C@@H](C2)[C@@](C4)(O)CO)C)C([C@H]([C@@H]1O)O)O
InChI InChI=1S/C26H42O9/c1-23-7-3-8-24(2,22(32)35-21-20(31)19(30)18(29)15(11-27)34-21)16(23)6-9-25-10-14(4-5-17(23)25)26(33,12-25)13-28/h14-21,27-31,33H,3-13H2,1-2H3/t14-,15?,16-,17-,18+,19-,20?,21-,23+,24+,25-,26-/m0/s1
InChIKey XKXZHTWOHXJEOL-OFUMLCJCSA-N
Formula C26H42O9
HBA 9
HBD 6
MW 498.61
Rotatable Bonds 4
TPSA 156.91
LogP 0.47
Number Rings 5
Number Aromatic Rings 0
Heavy Atom Count 35
Formal Charge 0
Fraction CSP3 0.96
Exact Mass 498.28
Number of Lipinski Rule Violations 1
# Species Family Kingdom NCBI Taxonomy ID
1 Pulicaria undulata Asteraceae Plantae 119186

Showing of synonyms

  • Abdel Bar F.M, Elsbaey M, et al. (2020). Phytochemical, antimicrobial and antiquorum-sensing studies of pulicaria undulata L.: a revision on the structure of 1b,2a,3b,19a,23-pentahydroxy-urs-12-en-28-oic acid. Natural product research, 2020, 34(6), 804-809. [View] [PubMed]

No compound-protein relationship available.

Structure

SMILES: O1CCCCC1OC(=O)C(CCC2)C(CC3)C2C(C345)CCC(C4)CC5

Level: 1

Mol. Weight: 498.61 g/mol

Structure

SMILES: C1CC(C2)CCC(C123)C4C(CC3)CCCC4

Level: 0

Mol. Weight: 498.61 g/mol

Structure

SMILES: C1CCOCC1

Level: 0

Mol. Weight: 498.61 g/mol

No bioactivities available.

Absorption

Caco-2 (logPapp)
-5.83
Human Oral Bioavailability 20%
Non-Bioavailable
Human Intestinal Absorption
Absorbed
Madin-Darby Canine Kidney
-5.03
Human Oral Bioavailability 50%
Bioavailable
P-Glycoprotein Inhibitor
Inhibitor
P-Glycoprotein Substrate
Non-Substrate
Skin Permeability
-1.35

Distribution

Blood-Brain Barrier (CNS)
-
Blood-Brain Barrier
Non-Penetrable
Fraction Unbound (Human)
0.87
Plasma Protein Binding
84.99
Steady State Volume of Distribution
-

Metabolism

Breast Cancer Resistance Protein
Non-Inhibitor
CYP 1A2 Inhibitor
Non-Inhibitor
CYP 1A2 Substrate
Non-Substrate
CYP 2C19 Inhibitor
Non-Inhibitor
CYP 2C19 Substrate
Non-Substrate
CYP 2C9 Inhibitor
Non-Inhibitor
CYP 2C9 Substrate
Non-Substrate
CYP 2D6 Inhibitor
Non-Inhibitor
CYP 2D6 Substrate
Non-Substrate
CYP 3A4 Inhibitor
Non-Inhibitor
CYP 3A4 Substrate
Substrate
OATP1B1
Non-Inhibitor
OATP1B3
Non-Inhibitor

Excretion

Clearance
-0.25
Organic Cation Transporter 2
Non-Inhibitor
Half-Life of Drug
-

Toxicity

AMES Mutagenesis
Safe
Avian
Safe
Bee
Toxic
Bioconcentration Factor
-4.06
Biodegradation
Safe
Carcinogenesis
Safe
Crustacean
Safe
Liver Injury I (DILI)
Toxic
Eye Corrosion
Safe
Eye Irritation
Safe
Maximum Tolerated Dose
-0.85
Liver Injury II
Safe
hERG Blockers
Safe
Daphnia Maga
5.36
Micronucleos
Safe
NR-AhR
Safe
NR-AR
Safe
NR-AR-LBD
Safe
NR-Aromatase
Safe
NR-ER
Safe
NR-ER-LBD
Safe
NR-GR
Safe
NR-PPAR-gamma
Safe
NR-TR
Safe
T. Pyriformis
-334.07
Rat (Acute)
3.41
Rat (Chronic Oral)
3.53
Fathead Minnow
3.64
Respiratory Disease
Toxic
Skin Sensitisation
Safe
SR-ARE
Safe
SR-ATAD5
Safe
SR-HSE
Safe
SR-MMP
Toxic
SR-p53
Safe

General Properties

Boiling Point
526.98
Hydration Free Energy
-3.02
Log(D) at pH=7.4
2.26
Log(P)
0.9
Log S
-2.7
Log(Vapor Pressure)
-13.13
Melting Point
210.92
pKa Acid
6.56
pKa Basic
6.85
Protein Name UniProt ID Entry Name Species #Pharmacophore Points Probability (0.7 ≤ Tversky Score ≤ 1.0)
Aldo-keto reductase family 1 member C2 P52895 AK1C2_HUMAN Homo sapiens 3 0.8178
Serpin domain-containing protein H0ZQY2 H0ZQY2_TAEGU Taeniopygia guttata 3 0.7784
Retinoic acid receptor RXR-alpha P19793 RXRA_HUMAN Homo sapiens 3 0.7436
Lactoylglutathione lyase Q9CPU0 LGUL_MOUSE Mus musculus 2 0.7392
2-aminohexano-6-lactam racemase Q7M181 ACLR_ACHOB Achromobacter obae 3 0.7135

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